Bis­(acridine-N)(nitrato-O,O′)silver(I)

The title complex, [Ag(NO₃)(C₁₃H₉N)₂], is the first complex of silver and acridine to be reported. The silver coordination is distorted trigonal. The N—Ag—N angle involving the N atoms of the acridine ligands is 145.84 (6)°. The nitrate ion coordinates to silver as an asymmetrically chelating bidentate ligand. The crystal structure consists of neutral complex mol­ecules linked into chains by means of attractive π–π interactions among the parallel acridine ligands.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: JANA2000 (Petricek & Dusek, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

Bis(acridine)(nitrato-O,O')silver(I)

Crystal data

[Ag(NO3)(C13H9N)2]	Z = 2
Mr = 528.30	F(000) = 532
Triclinic, P1	Dx = 1.711 Mg m^−3
a = 9.128 (3) Å	Mo Kα radiation, λ = 0.71069 Å
b = 10.096 (2) Å	Cell parameters from 25 reflections
c = 11.763 (2) Å	θ = 12–13°
α = 108.19 (1)°	µ = 1.02 mm^−1
β = 91.93 (2)°	T = 293 K
γ = 94.23 (2)°	Prism with strongly rounded edges, translucent intense brown
V = 1025.2 (4) Å^3	0.20 × 0.15 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3466 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
background–peak–background scans	h = 0→10
Absorption correction: spherical (JANA2000; Petricek & Dusek, 2000)	k = −11→11
Tmin = 0.793, Tmax = 0.797	l = −13→13
3593 measured reflections	3 standard reflections every 60 min
3593 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.0269P)^2 + 0.7513P] where P = (Fo^2 + 2Fc^2)/3
S = 1.19	(Δ/σ)max = 0.002
3593 reflections	Δρmax = 0.58 e Å^−3
335 parameters	Δρmin = −0.72 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: heavy-atom method	Extinction coefficient: 0.0035 (7)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ag	0.102005 (16)	−0.059315 (15)	0.763808 (14)	0.02333 (8)
N1D	0.01666 (18)	−0.27270 (18)	0.88422 (16)	0.0226 (4)
O2D	0.0280 (2)	−0.31216 (18)	0.77284 (15)	0.0366 (4)
O3D	0.02457 (19)	−0.14307 (16)	0.93871 (15)	0.0325 (4)
O4D	−0.0019 (2)	−0.35780 (18)	0.93934 (16)	0.0376 (4)
N1A	0.34197 (18)	−0.02535 (18)	0.81562 (15)	0.0185 (3)
C2A	0.4336 (2)	−0.1265 (2)	0.76894 (18)	0.0192 (4)
C3A	0.3745 (2)	−0.2575 (2)	0.68879 (19)	0.0239 (4)
H3A	0.277 (3)	−0.2732 (5)	0.6707 (6)	0.027 (6)*
C4A	0.4644 (3)	−0.3602 (2)	0.6388 (2)	0.0275 (5)
H4A	0.4218 (13)	−0.450 (3)	0.5833 (17)	0.039 (7)*
C5A	0.6181 (3)	−0.3380 (2)	0.6662 (2)	0.0275 (5)
H5A	0.6794 (18)	−0.409 (2)	0.6294 (11)	0.033 (7)*
C6A	0.6780 (2)	−0.2157 (2)	0.7449 (2)	0.0247 (5)
H6A	0.779 (3)	−0.2033 (4)	0.7639 (6)	0.031 (7)*
C7A	0.5885 (2)	−0.1055 (2)	0.79918 (18)	0.0205 (4)
C8A	0.6455 (2)	0.0222 (2)	0.88053 (19)	0.0220 (4)
H8A	0.746 (3)	0.0371 (5)	0.9035 (7)	0.023 (6)*
C9A	0.5535 (2)	0.1274 (2)	0.92762 (18)	0.0207 (4)
C10A	0.6057 (2)	0.2616 (2)	1.0090 (2)	0.0255 (5)
H10A	0.707 (3)	0.2813 (6)	1.0331 (7)	0.027 (6)*
C11A	0.5116 (3)	0.3610 (2)	1.0521 (2)	0.0270 (5)
H11A	0.5483 (11)	0.451 (3)	1.1055 (16)	0.032 (7)*
C12A	0.3594 (3)	0.3322 (2)	1.01846 (19)	0.0258 (5)
H12A	0.294 (2)	0.403 (2)	1.0496 (10)	0.037 (7)*
C13A	0.3045 (2)	0.2052 (2)	0.94223 (18)	0.0228 (4)
H13A	0.205 (3)	0.1880 (5)	0.9224 (6)	0.023 (6)*
C14A	0.3998 (2)	0.0990 (2)	0.89289 (17)	0.0187 (4)
N1B	−0.07387 (18)	−0.03849 (18)	0.63764 (15)	0.0189 (3)
C2B	−0.1451 (2)	0.0799 (2)	0.66188 (18)	0.0191 (4)
C3B	−0.1034 (2)	0.1925 (2)	0.76843 (19)	0.0224 (4)
H3B	−0.028 (2)	0.1838 (3)	0.8206 (15)	0.023 (6)*
C4B	−0.1717 (2)	0.3129 (2)	0.7951 (2)	0.0262 (5)
H4B	−0.1422 (10)	0.385 (2)	0.863 (2)	0.033 (7)*
C5B	−0.2885 (3)	0.3271 (2)	0.7183 (2)	0.0294 (5)
H5B	−0.3372 (15)	0.412 (3)	0.7389 (7)	0.038 (7)*
C6B	−0.3322 (2)	0.2221 (2)	0.6163 (2)	0.0271 (5)
H6B	−0.410 (2)	0.2331 (4)	0.5660 (15)	0.028 (6)*
C7B	−0.2615 (2)	0.0946 (2)	0.58363 (18)	0.0215 (4)
C8B	−0.3010 (2)	−0.0157 (2)	0.47952 (19)	0.0236 (4)
H8B	−0.375 (2)	−0.0082 (3)	0.4285 (15)	0.023 (6)*
C9B	−0.2288 (2)	−0.1376 (2)	0.45232 (18)	0.0211 (4)
C10B	−0.2632 (2)	−0.2535 (2)	0.3462 (2)	0.0271 (5)
H10B	−0.337 (2)	−0.2498 (3)	0.2926 (17)	0.034 (7)*
C11B	−0.1881 (3)	−0.3694 (2)	0.3232 (2)	0.0299 (5)
H11B	−0.2107 (7)	−0.443 (2)	0.253 (2)	0.032 (7)*
C12B	−0.0756 (3)	−0.3776 (2)	0.4058 (2)	0.0281 (5)
H12B	−0.0245 (16)	−0.459 (3)	0.3894 (6)	0.039 (7)*
C13B	−0.0396 (2)	−0.2695 (2)	0.5089 (2)	0.0239 (4)
H13B	0.033 (2)	−0.2769 (3)	0.5616 (16)	0.025 (6)*
C14B	−0.1142 (2)	−0.1452 (2)	0.53526 (18)	0.0192 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag	0.01686 (10)	0.02092 (11)	0.02971 (11)	0.00245 (6)	−0.00459 (6)	0.00486 (7)
N1D	0.0163 (9)	0.0223 (9)	0.0276 (10)	0.0022 (7)	−0.0009 (7)	0.0060 (8)
O2D	0.0476 (11)	0.0311 (9)	0.0272 (9)	0.0082 (8)	0.0094 (8)	0.0019 (7)
O3D	0.0415 (10)	0.0201 (8)	0.0308 (9)	−0.0011 (7)	0.0023 (7)	0.0016 (7)
O4D	0.0452 (10)	0.0298 (9)	0.0415 (10)	−0.0025 (8)	−0.0031 (8)	0.0185 (8)
N1A	0.0165 (8)	0.0222 (9)	0.0170 (8)	0.0031 (7)	0.0011 (6)	0.0062 (7)
C2A	0.0178 (10)	0.0248 (11)	0.0175 (9)	0.0037 (8)	0.0025 (8)	0.0096 (8)
C3A	0.0202 (11)	0.0279 (11)	0.0216 (10)	0.0043 (9)	0.0004 (8)	0.0048 (9)
C4A	0.0330 (12)	0.0263 (12)	0.0212 (10)	0.0068 (9)	0.0043 (9)	0.0037 (9)
C5A	0.0304 (12)	0.0311 (12)	0.0253 (11)	0.0140 (10)	0.0117 (9)	0.0113 (9)
C6A	0.0181 (11)	0.0342 (12)	0.0288 (11)	0.0079 (9)	0.0073 (9)	0.0178 (10)
C7A	0.0181 (10)	0.0267 (11)	0.0212 (10)	0.0043 (8)	0.0041 (8)	0.0131 (9)
C8A	0.0149 (10)	0.0312 (12)	0.0244 (11)	−0.0008 (8)	0.0007 (8)	0.0159 (9)
C9A	0.0203 (10)	0.0252 (11)	0.0195 (10)	−0.0012 (8)	0.0006 (8)	0.0118 (8)
C10A	0.0227 (11)	0.0290 (12)	0.0262 (11)	−0.0055 (9)	−0.0028 (9)	0.0127 (9)
C11A	0.0349 (13)	0.0216 (11)	0.0231 (11)	−0.0034 (9)	−0.0027 (9)	0.0069 (9)
C12A	0.0311 (12)	0.0238 (11)	0.0228 (11)	0.0052 (9)	0.0022 (9)	0.0072 (9)
C13A	0.0202 (11)	0.0262 (11)	0.0212 (10)	0.0035 (8)	−0.0006 (8)	0.0064 (9)
C14A	0.0185 (10)	0.0229 (10)	0.0167 (9)	0.0012 (8)	0.0010 (8)	0.0092 (8)
N1B	0.0154 (8)	0.0189 (8)	0.0224 (9)	0.0005 (6)	0.0019 (7)	0.0067 (7)
C2B	0.0160 (9)	0.0206 (10)	0.0230 (10)	0.0011 (8)	0.0057 (8)	0.0098 (8)
C3B	0.0182 (10)	0.0224 (11)	0.0256 (11)	0.0005 (8)	0.0012 (9)	0.0065 (9)
C4B	0.0284 (12)	0.0216 (11)	0.0279 (11)	0.0025 (9)	0.0058 (9)	0.0065 (9)
C5B	0.0322 (12)	0.0250 (12)	0.0356 (13)	0.0120 (10)	0.0096 (10)	0.0132 (10)
C6B	0.0229 (11)	0.0336 (13)	0.0308 (12)	0.0098 (9)	0.0047 (9)	0.0169 (10)
C7B	0.0179 (10)	0.0267 (11)	0.0237 (10)	0.0038 (8)	0.0060 (8)	0.0127 (9)
C8B	0.0170 (10)	0.0342 (12)	0.0226 (10)	0.0022 (9)	0.0004 (8)	0.0131 (9)
C9B	0.0173 (10)	0.0271 (11)	0.0199 (10)	−0.0014 (8)	0.0034 (8)	0.0092 (9)
C10B	0.0224 (11)	0.0370 (13)	0.0200 (10)	−0.0007 (9)	−0.0006 (9)	0.0073 (9)
C11B	0.0313 (12)	0.0285 (12)	0.0233 (11)	−0.0026 (9)	0.0031 (9)	−0.0004 (10)
C12B	0.0293 (12)	0.0231 (11)	0.0295 (12)	0.0039 (9)	0.0071 (9)	0.0040 (9)
C13B	0.0219 (11)	0.0238 (11)	0.0254 (11)	0.0029 (8)	0.0009 (9)	0.0069 (9)
C14B	0.0164 (9)	0.0216 (10)	0.0201 (10)	−0.0007 (8)	0.0045 (8)	0.0075 (8)

Geometric parameters (Å, º)

Ag—N1B	2.216 (2)	C12A—H12A	0.9533
Ag—N1A	2.226 (2)	C13A—C14A	1.424 (3)
Ag—O2D	2.627 (2)	C13A—H13A	0.9204
Ag—O3D	2.558 (2)	N1B—C2B	1.359 (3)
N1D—O4D	1.233 (2)	N1B—C14B	1.359 (3)
N1D—O2D	1.255 (2)	C2B—C3B	1.422 (3)
N1D—O3D	1.260 (2)	C2B—C7B	1.429 (3)
N1A—C14A	1.356 (3)	C3B—C4B	1.360 (3)
N1A—C2A	1.360 (3)	C3B—H3B	0.9320
C2A—C3A	1.418 (3)	C4B—C5B	1.418 (3)
C2A—C7A	1.430 (3)	C4B—H4B	0.9087
C3A—C4A	1.368 (3)	C5B—C6B	1.355 (3)
C3A—H3A	0.8977	C5B—H5B	0.9637
C4A—C5A	1.415 (3)	C6B—C7B	1.432 (3)
C4A—H4A	0.9810	C6B—H6B	0.9456
C5A—C6A	1.354 (3)	C7B—C8B	1.389 (3)
C5A—H5A	0.9475	C8B—C9B	1.392 (3)
C6A—C7A	1.428 (3)	C8B—H8B	0.9112
C6A—H6A	0.9300	C9B—C10B	1.427 (3)
C7A—C8A	1.395 (3)	C9B—C14B	1.429 (3)
C8A—C9A	1.392 (3)	C10B—C11B	1.358 (3)
C8A—H8A	0.9344	C10B—H10B	0.9188
C9A—C10A	1.429 (3)	C11B—C12B	1.415 (3)
C9A—C14A	1.430 (3)	C11B—H11B	0.9252
C10A—C11A	1.356 (3)	C12B—C13B	1.365 (3)
C10A—H10A	0.9462	C12B—H12B	0.9467
C11A—C12A	1.416 (3)	C13B—C14B	1.425 (3)
C11A—H11A	0.9567	C13B—H13B	0.9141
C12A—C13A	1.362 (3)
N1B—Ag—N1A	145.84 (6)	C14A—C13A—H13A	119.7
N1B—Ag—O3D	117.72 (6)	N1A—C14A—C13A	119.07 (18)
N1A—Ag—O3D	96.31 (6)	N1A—C14A—C9A	122.40 (18)
N1B—Ag—O2D	101.09 (6)	C13A—C14A—C9A	118.53 (19)
N1A—Ag—O2D	103.64 (6)	C2B—N1B—C14B	118.76 (18)
O4D—N1D—O2D	121.27 (18)	C2B—N1B—Ag	120.79 (14)
O4D—N1D—O3D	120.60 (18)	C14B—N1B—Ag	120.44 (13)
O2D—N1D—O3D	118.13 (18)	N1B—C2B—C3B	119.26 (19)
N1D—O3D—Ag	97.62 (12)	N1B—C2B—C7B	121.91 (19)
C14A—N1A—C2A	118.77 (17)	C3B—C2B—C7B	118.83 (19)
C14A—N1A—Ag	120.03 (13)	C4B—C3B—C2B	120.8 (2)
C2A—N1A—Ag	121.17 (14)	C4B—C3B—H3B	119.6
N1A—C2A—C3A	119.40 (19)	C2B—C3B—H3B	119.6
N1A—C2A—C7A	121.99 (19)	C3B—C4B—C5B	120.5 (2)
C3A—C2A—C7A	118.60 (19)	C3B—C4B—H4B	119.8
C4A—C3A—C2A	120.7 (2)	C5B—C4B—H4B	119.8
C4A—C3A—H3A	119.7	C6B—C5B—C4B	120.6 (2)
C2A—C3A—H3A	119.7	C6B—C5B—H5B	119.7
C3A—C4A—C5A	120.7 (2)	C4B—C5B—H5B	119.7
C3A—C4A—H4A	119.7	C5B—C6B—C7B	120.8 (2)
C5A—C4A—H4A	119.7	C5B—C6B—H6B	119.6
C6A—C5A—C4A	120.3 (2)	C7B—C6B—H6B	119.6
C6A—C5A—H5A	119.8	C8B—C7B—C2B	118.41 (19)
C4A—C5A—H5A	119.8	C8B—C7B—C6B	123.1 (2)
C5A—C6A—C7A	120.9 (2)	C2B—C7B—C6B	118.5 (2)
C5A—C6A—H6A	119.5	C7B—C8B—C9B	120.7 (2)
C7A—C6A—H6A	119.5	C7B—C8B—H8B	119.6
C8A—C7A—C6A	122.9 (2)	C9B—C8B—H8B	119.6
C8A—C7A—C2A	118.38 (19)	C8B—C9B—C10B	123.3 (2)
C6A—C7A—C2A	118.8 (2)	C8B—C9B—C14B	117.79 (19)
C9A—C8A—C7A	120.3 (2)	C10B—C9B—C14B	118.94 (19)
C9A—C8A—H8A	119.9	C11B—C10B—C9B	120.9 (2)
C7A—C8A—H8A	119.9	C11B—C10B—H10B	119.5
C8A—C9A—C10A	123.0 (2)	C9B—C10B—H10B	119.5
C8A—C9A—C14A	118.15 (19)	C10B—C11B—C12B	120.2 (2)
C10A—C9A—C14A	118.87 (19)	C10B—C11B—H11B	119.9
C11A—C10A—C9A	120.8 (2)	C12B—C11B—H11B	119.9
C11A—C10A—H10A	119.6	C13B—C12B—C11B	120.9 (2)
C9A—C10A—H10A	119.6	C13B—C12B—H12B	119.5
C10A—C11A—C12A	120.2 (2)	C11B—C12B—H12B	119.5
C10A—C11A—H11A	119.9	C12B—C13B—C14B	120.6 (2)
C12A—C11A—H11A	119.9	C12B—C13B—H13B	119.7
C13A—C12A—C11A	121.0 (2)	C14B—C13B—H13B	119.7
C13A—C12A—H12A	119.5	N1B—C14B—C13B	119.10 (19)
C11A—C12A—H12A	119.5	N1B—C14B—C9B	122.42 (19)
C12A—C13A—C14A	120.6 (2)	C13B—C14B—C9B	118.48 (19)
C12A—C13A—H13A	119.7
O4D—N1D—O3D—Ag	171.50 (16)	C8A—C9A—C14A—C13A	178.93 (18)
O2D—N1D—O3D—Ag	−8.55 (19)	C10A—C9A—C14A—C13A	−0.8 (3)
N1B—Ag—O3D—N1D	85.13 (13)	N1A—Ag—N1B—C2B	−90.02 (17)
N1A—Ag—O3D—N1D	−97.84 (13)	O3D—Ag—N1B—C2B	84.71 (15)
N1B—Ag—N1A—C14A	88.05 (17)	N1A—Ag—N1B—C14B	91.05 (17)
O3D—Ag—N1A—C14A	−87.26 (14)	O3D—Ag—N1B—C14B	−94.22 (15)
N1B—Ag—N1A—C2A	−90.41 (18)	C14B—N1B—C2B—C3B	−179.70 (17)
O3D—Ag—N1A—C2A	94.28 (15)	Ag—N1B—C2B—C3B	1.4 (2)
C14A—N1A—C2A—C3A	179.48 (18)	C14B—N1B—C2B—C7B	0.6 (3)
Ag—N1A—C2A—C3A	−2.0 (2)	Ag—N1B—C2B—C7B	−178.30 (14)
C14A—N1A—C2A—C7A	0.2 (3)	N1B—C2B—C3B—C4B	179.58 (19)
Ag—N1A—C2A—C7A	178.65 (14)	C7B—C2B—C3B—C4B	−0.7 (3)
N1A—C2A—C3A—C4A	178.79 (19)	C2B—C3B—C4B—C5B	1.5 (3)
C7A—C2A—C3A—C4A	−1.9 (3)	C3B—C4B—C5B—C6B	−1.1 (3)
C2A—C3A—C4A—C5A	0.2 (3)	C4B—C5B—C6B—C7B	0.0 (3)
C3A—C4A—C5A—C6A	1.6 (3)	N1B—C2B—C7B—C8B	−0.6 (3)
C4A—C5A—C6A—C7A	−1.7 (3)	C3B—C2B—C7B—C8B	179.70 (18)
C5A—C6A—C7A—C8A	−179.9 (2)	N1B—C2B—C7B—C6B	179.27 (18)
C5A—C6A—C7A—C2A	0.0 (3)	C3B—C2B—C7B—C6B	−0.4 (3)
N1A—C2A—C7A—C8A	1.0 (3)	C5B—C6B—C7B—C8B	−179.3 (2)
C3A—C2A—C7A—C8A	−178.31 (18)	C5B—C6B—C7B—C2B	0.8 (3)
N1A—C2A—C7A—C6A	−178.92 (18)	C2B—C7B—C8B—C9B	0.1 (3)
C3A—C2A—C7A—C6A	1.8 (3)	C6B—C7B—C8B—C9B	−179.80 (19)
C6A—C7A—C8A—C9A	177.93 (19)	C7B—C8B—C9B—C10B	−179.22 (19)
C2A—C7A—C8A—C9A	−2.0 (3)	C7B—C8B—C9B—C14B	0.4 (3)
C7A—C8A—C9A—C10A	−178.46 (19)	C8B—C9B—C10B—C11B	179.2 (2)
C7A—C8A—C9A—C14A	1.8 (3)	C14B—C9B—C10B—C11B	−0.4 (3)
C8A—C9A—C10A—C11A	179.8 (2)	C9B—C10B—C11B—C12B	1.0 (3)
C14A—C9A—C10A—C11A	−0.5 (3)	C10B—C11B—C12B—C13B	−0.6 (3)
C9A—C10A—C11A—C12A	1.1 (3)	C11B—C12B—C13B—C14B	−0.5 (3)
C10A—C11A—C12A—C13A	−0.3 (3)	C2B—N1B—C14B—C13B	179.72 (18)
C11A—C12A—C13A—C14A	−1.1 (3)	Ag—N1B—C14B—C13B	−1.3 (2)
C2A—N1A—C14A—C13A	−179.90 (18)	C2B—N1B—C14B—C9B	−0.1 (3)
Ag—N1A—C14A—C13A	1.6 (2)	Ag—N1B—C14B—C9B	178.82 (14)
C2A—N1A—C14A—C9A	−0.4 (3)	C12B—C13B—C14B—N1B	−178.81 (19)
Ag—N1A—C14A—C9A	−178.88 (14)	C12B—C13B—C14B—C9B	1.0 (3)
C12A—C13A—C14A—N1A	−178.86 (19)	C8B—C9B—C14B—N1B	−0.4 (3)
C12A—C13A—C14A—C9A	1.6 (3)	C10B—C9B—C14B—N1B	179.23 (18)
C8A—C9A—C14A—N1A	−0.6 (3)	C8B—C9B—C14B—C13B	179.77 (19)
C10A—C9A—C14A—N1A	179.64 (18)	C10B—C9B—C14B—C13B	−0.6 (3)